Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate
P. Veeraraghavan Ramachandran* and Prem B. Chanda
*Herbert C. Brown Center for Borane Research, Department of
Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana
47907-2084, United States, Email: chandranpurdue.edu
P. V. Ramachandran, P. B. Chanda, Org. Lett., 2012, 14, 4346-4349.
DOI: 10.1021/ol301782s
Abstract
The choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl2, the reaction favors the anti-pathway at -78 °C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.
see article for more examples
A. Y. Thomas, T. L. Walls III, B. N. Nelson, S. W. Primeaux, P. B. Chanda, J. Org. Chem., 2021, 86, 6184-6194.
Key Words
ID: J54-Y2012-2790